You must be referencing a court case where a modern warrant canary has ended with the perp in jail. Who might that be? You prefaced with "I think", but spoke with quite steadfast certainty, surely this piqued your interest for a reason.
No, nothing specifically related to Warrant Canaries but some law podcasts I listened to - ALAB and Mic Dicta for example - have referenced this phenomenon a few times. It's usually a tech bro or sovereign citizen with a novel interpretation of a law that ends up failing when they eventually have to try to argue their case it in court.
True, and it's been elaborated elsewhere that these have already been tested in the supreme court. But you have to admit that without that precedent, it does seem a little bit cheeky - "oh the law says I can't do X, well it doesn't say I can't simply not do inverse(X)" :)
For a funny / not funny example, see the attempts to ban analogs of illegal drugs. The whole research chemical thing is a result of the need to legislate exactly what’s illegal.
Supreme Court decisions can sound like sovcit stuff when they reference English common law, the Magna Carta, etc. Warrant canaries are just intended to exploit a technicality. There are a lot of technicalities in law that authoritarians don't like.
